Transsexual son haunts Hemingway clan

In life, Ernest Hemingway's son Gregory was a tortured character, a furtive cross-dresser ridiculed by his macho father who later had a sex-change operation but never overcame a lifelong struggle with manic depression. He died two years ago, ignominiously, in the women's annex of the Miami-Dade county jail in Florida where he had been booked for ambling, drunk and near-naked, down a street in Key Biscayne.

Now, the family conflict and psychosexual drama that haunted him - or her - have carried over beyond the grave. The last of his four wives and five of his eight children are battling over his estate in court, and his sex change could well prove to be the key to resolving the case.

Just as he had two genders, Gregory Hemingway (or Gloria, as he also called himself) wrote two wills. The first left the bulk of his inherited wealth - about $7m (£4m) - to his children. The second, by contrast, named his wife Ida as chief beneficiary. Ida Hemingway's argument is that the first will was written when she and Gregory were in the midst of a break-up - they divorced in 1995 but then remarried in 1997. The second will was meant as a correction of the earlier decision to cut her off.

The childrens' argument is where the case gets really intriguing. Their lawyers point out that at the time of Gregory and Ida's remarriage, Gregory had already had his sex change (which took place shortly after the divorce, in 1995). Since Florida does not recognise same-sex marriages, they argue, the union is invalid and, by the same token, invalidates all claims Ida might have to inherit as spouse of the deceased.

It seems to be a classic case of the US court system reducing even the most tormented and touching family drama to utter farce. Judge Arthur Rothenberg, presiding over the mess, is expected to rule shortly on the validity of the second will. Both sides have filed briefs on the subject, to add to hundreds of pages of legal documents already submitted in the case.

The dispute smacks of a squalid end to a singularly unhappy life. Ironically, Gregory Hemingway regarded him- self in later life as near broke, having lost medical licences in two states because of his drinking and constant run-ins with the law. At one point in the 1990s he was sleeping in a dilapidated Volkswagen. When he went ahead with the sex change, he was so parsimonious about the cost that for several months he went around with only one breast.

His was an extraordinary story from the outset. When he was born, in 1931, Ernest Hemingway was yearning for a girl. The young Gregory, or Gig, as he was known, made gargantuan efforts to please his father, becoming an accomplished elephant hunter, an academic high achiever and an elegant writer who later penned the autobiographical Papa: A Personal Memoir.

When his father discovered his transvestite tendencies - catching Gig in the act of trying on his stepmother Martha Gellhorn's dresses and tights - he was furious. Gig went into therapy and later underwent drastic psychiatric interventions including several bouts of electric shock therapy.

"I've spent hundreds of thousands of dollars trying not to be a transvestite," he once said. "It's a combination of things - first you've got this father who's super-masculine but who's somehow protesting it all the time. He's worried to death about it."

At the time of his final arrest, Gregory/Gloria was described as euphoric about the successful introduction of his female persona to some Miami friends. Within 24 hours of a coming-out party, however, "she" was drunk, tottering on a Key Biscayne street with a hospital gown draped over her shoulders and attempting to change out of a dress into a flowered thong.

Although bail was set at just $2,000, nobody sprang him from jail. His family later accused the authorities of failing to give him his hypertension medication. The coroner ruled that he died of a heart attack.